Macromolecular Research, Vol.23, No.4, 341-349, April, 2015
Photopolymerization kinetic studies of UV-curable sulfur-containing difunctional acrylate monomers using photo-DSC
E-mail:
We synthesized UV-curable difunctional sulfur-containing thioacrylate and thiourethane acrylate with high refractive indices. The monomer structures were confirmed by nuclear magnetic resonance (NMR) spectroscopy and Fourier transform infrared spectroscopy (FTIR). The photopolymerization kinetics of 3,3′-thiobis(1-(phenylthio)propane-3,2-diyl) diacrylate (SMDA) and 4,12-dioxo-6,10-bis(phenylthiomethyl)-3,13-dioxa-8-thia-5,11-diazapentadecane-1,15-diyl diacrylate (SMUA) were investigated by photo-differential scanning calorimetry (photo-DSC). The effects of various parameters such as the UV intensity, temperature, photoinitiator concentration, and the type of initiator were evaluated. In SMDA, as the temperature and light intensity increased, the peak maximum time tended to decrease. The conversion increased with increasing temperature up to 60 °C and light intensity up to 20 mW/cm2. The highest polymerization conversion was achieved with a PI concentration of 2.5% (w/w) with BK-6 as the PI. In SMUA, the rate of photopolymerization reached to the maximum value at 60 °C and 20 mW/cm2. For the PI concentration, the maximum conversion and polymerization rate constant were the highest with 2.5% (w/w). Also the highest conversion of polymerization was achieved using HP-8 as the PI. The activation energies of SMDA and SMUA were 3.95 and 36.01 kJ/mol, respectively.
- Rabek JF, Mechanisms of Photophysical abd Photochemcial Reactions in Polymers, Theory and Practical Applications, Wiley, New York, 1987.
- Hwang H, Park C, Moon J, Kim H, Masubuchi T, Prog. Org. Coat., 72, 663 (2011)
- Fieberg A, Reis O, Prog. Org. Coat., 45, 239 (2002)
- Decker C, Macromol. Rapid Commun., 23(18), 1067 (2002)
- Lowe C, Oldring PKT, Chemistry and Technology of UV and EB Formulations for Coatings, Inks and Paints, Vol. IV, SITA Press, London, 1991.
- Karagoz B, Bicak N, Eur. Polym. J., 44, 106 (2008)
- Nakamura A, Fujii H, Juni N, Tsutsumi N, Opt. Rev., 1, 104 (2008)
- Nebioglu A, Leon JA, Khudyakov IV, Ind. Eng. Chem. Res., 47(7), 2155 (2008)
- Liu JG, Ueda M, J. Mater. Chem., 19, 8907 (2009)
- Ando S, Fujigaya T, Ueda M, Jpn. J. Appl. Phys., 41, L105 (2002)
- Matsuda T, Funae Y, Yoshida M, Yamamoto T, Takaya T, J. Appl. Polym. Sci., 76(1), 50 (2000)
- Okutsu R, Suzuki Y, Ando S, Ueda M, Macromolecules, 41(16), 6165 (2008)
- Hidehiko A, Katsumasa Y, JP Patent 2013155118 (2013).
- Kim JS, Cho BS, Kweon JO, Noh ST, Prog. Org. Coat., 77, 1695 (2014)
- Suwa M, Niwa H, Tomikawa MJ, Polym. Sci. Technol., 19, 275 (2006)
- Nakai J, Aoki T, US Patent 7087945 (2006).
- Mori K, Tano T, JP Patent 2007056048 (2007).
- Decker C, Acta Polym., 45, 333 (1994)
- Kloosterboer JG, Adv. Polym. Sci., 84, 1 (1998)
- Corcione CE, Greco A, Maffezzoli A, Polymer, 46(19), 8018 (2005)
- Avci D, Nobles J, Mathias LJ, Polymer, 44, 960 (2003)
- Scott TF, Cook WD, Forsythe JS, Polymer, 44(3), 671 (2003)
- Doornkamp T, Tan YY, Polym. Commun., 31, 362 (1990)
- Scherzer T, Decker U, Vib. Spectrosc., 19, 385 (1999)
- Dworak DP, Soucek MD, Prog. Org. Coat., 47, 448 (2003)
- Scott TF, Cook WD, Forsythe JS, Polymer, 43(22), 5839 (2002)
- Anseth KS, Wang CM, Bowman CN, Polymer, 35(15), 3243 (1994)
- Young JS, Bowman CN, Macromolecules, 32(19), 6073 (1999)
- Cook WD, J. Polym. Sci. A: Polym. Chem., 31, 1053 (1993)
- Corcione CE, Frigione M, Thermochim. Acta, 534, 21 (2012)
- Corcione CE, Previderio A, Frigione M, Thermochim. Acta, 509(1-2), 56 (2010)
- Corcione CE, Greco A, Maffezzoli A, J. Appl. Polym. Sci., 92(6), 3484 (2004)
- Andrzejewska E, Andrzejewski M, J. Polym. Sci. A: Polym. Chem., 36(4), 665 (1998)
- Maffezzoli A, Terzi R, Thermochim. Acta, 321(1-2), 111 (1998)
- Nelson EW, Jacobs JL, Scranton AB, Anseth KS, Bowman CN, Polymer, 36(24), 4651 (1995)
- Castell P, Wouters M, Fischer H, de with G, J. Coat. Technol. Res., 4, 411 (2007)
- Andrzejewska E, Polymer, 37(6), 1047 (1996)
- Broer DJ, Mol GN, Challa G, Polymer, 32, 690 (1991)